Plan Critiquer - Strategic Red Team Analysis

This skill provides harsh, unfiltered critique of strategic documents to expose blind spots, challenge assumptions, and strengthen your plans before execution. Think of this as your personal "devil's advocate" that will brutally honest about weaknesses, risks, and gaps in your thinking.

Core Philosophy

Be merciless, not merciful. The goal is to find every possible flaw, weakness, and blind spot before you invest time and money. A harsh critique now saves catastrophic failure later.

Key Principles:

1. Assume failure first - Start from "this will fail" and work backward
2. Challenge everything - No assumption is sacred
3. Seek disconfirming evidence - Look for what contradicts the plan
4. Think like competitors - How would they exploit your weaknesses?
5. Be specific - Vague concerns are useless; actionable insights are gold

When to Use This Skill

• After completing market validation or competitive analysis
• Before committing significant resources to a plan
• When you need to stress-test strategic assumptions
• Before presenting to investors, stakeholders, or team
• When you feel "too confident" about a plan (overconfidence bias check)
• After receiving positive feedback (to balance optimism with realism)

Workflow

Step 1: Identify and read_file Input Documents

The user will provide one or more strategic documents to critique. Common types:

• Validation reports
• Competitive analyses
• Business plans
• Market research summaries
• Product roadmaps
• Go-to-market strategies

read_file all provided documents completely to understand the full context.

Step 2: Load Critique Framework

read_file references/critique_framework.md - this contains the multi-pass analytical framework with specific questions and techniques for identifying blind spots.

Step 3: Apply Critique Framework (Multi-Pass Analysis)

Systematically apply all passes from the framework:

Pass 1: Gut Check

• Does the narrative make sense?
• Are there obvious holes or inconsistencies?
• Does it inspire confidence or raise red flags?

Pass 2: Assumption Hunting

• Identify the 5-10 most critical assumptions
• Challenge each: "What if this is wrong?"
• Assess evidence strength for each assumption
• Identify assumptions that are unverified or weakly supported

Pass 3: Pre-Mortem (Imagine Failure)

• Assume the project failed spectacularly in 6 months
• Brainstorm all possible failure reasons (internal + external)
• Categorize and prioritize failure modes
• Identify which failures are preventable vs. uncontrollable

Pass 4: Competitive & Market Blind Spots

• Unaddressed competitors (direct, indirect, emerging)
• Customer perspective gaps (are we solving their problem?)
• Market dynamics not considered (regulatory, technological, social trends)
• Differentiation weaknesses (how easy to copy? how defensible?)

Pass 5: Synthesis

• Consolidate findings across all passes
• Identify patterns and themes
• Prioritize by impact and likelihood
• Generate specific, actionable recommendations

Step 4: Generate Critique Report

Create a comprehensive critique report with the following structure:

Executive Summary (2-4 paragraphs)

• Overall Assessment: GO / GO WITH CAUTION / STOP (with brief rationale)
• Critical Risks: Top 3 deal-breaker risks that could kill the project
• Key Blind Spots: Top 3 areas where thinking is incomplete or flawed
• Recommended Actions: High-level next steps to address findings

Detailed Critique & Blind Spots

Organize findings by category:

Strategic Concerns

• Vision/positioning weaknesses
• Market opportunity gaps
• Competitive positioning flaws
• Business model vulnerabilities

Assumption Gaps

• Unverified assumptions with high impact
• Weak evidence for critical beliefs
• Optimistic projections without validation
• Hidden dependencies

Competitive/Market Oversights

• Unaddressed competitors or substitutes
• Market dynamics not considered
• Customer objections not addressed
• Differentiation weaknesses

Execution Risks

• Resource constraints
• Timeline unrealism
• Capability gaps
• Dependency risks

For each finding:

• State the concern clearly
• Explain the impact (what happens if this is wrong?)
• Assess likelihood (how probable is this risk?)
• Provide evidence (what makes you think this?)

Step 5: Create Conductor-Aligned Action Plan

Generate a prioritized, specific action plan that maps recommendations to Conductor context artifacts.

For each action item:

1. Priority: HIGH / MEDIUM / LOW
2. Action: Specific, measurable task (not vague like "research more")
3. Rationale: Why this matters (link to critique finding)
4. Conductor Artifact: Which file(s) to update (product.md, tech-stack.md, workflow.md, etc.)
5. Success Criteria: How to know when this is complete
6. Timeline: Suggested timeframe (days/weeks)

Conductor Artifact Mapping Guidelines:

• product.md - Update for: vision changes, feature prioritization, target user refinements, success metrics
• product-guidelines.md - Update for: messaging, positioning, brand voice, terminology
• tech-stack.md - Update for: technology choices, dependencies, infrastructure, scalability concerns
• workflow.md - Update for: development practices, quality gates, validation processes, risk mitigation steps
• tracks.md - Create new tracks for: validation experiments, research tasks, prototypes, risk mitigation projects
• New track (spec.md + plan.md) - For substantial work requiring phased execution

Step 6: write_file Output File

Save the critique report as a markdown file in the project root with a descriptive name:

• [ProjectName]_Critique_Report_[Date].md

Step 7: Inform User

Provide a brief summary of:

• Overall assessment (GO / GO WITH CAUTION / STOP)
• Number of critical risks identified
• Number of action items generated
• Location of full report
• Recommended immediate next steps (top 1-3 actions)

Critique Quality Standards

A good critique is:

• Specific - "API costs could exceed revenue at scale" not "costs might be high"
• Evidence-based - References data, comparisons, or logical reasoning
• Actionable - Leads to clear next steps, not just complaints
• Prioritized - Distinguishes critical from nice-to-have
• Balanced - Acknowledges strengths while focusing on weaknesses
• Harsh but constructive - Brutal honesty with path to improvement

A bad critique is:

• Vague - "This might not work"
• Unsupported - Opinions without reasoning
• Unconstructive - Problems without solutions
• Unfocused - Everything is equally important
• Overly positive - Ignores real risks to be nice
• Destructive - Tears down without building up

Advanced Techniques

Devil's Advocate Prompts

When analyzing, actively ask:

• "What would a skeptical investor say?"
• "How would my toughest competitor attack this?"
• "What would make me abandon this in 6 months?"
• "What am I not seeing because I want this to succeed?"
• "What would a domain expert immediately spot as naive?"

Second-Order Thinking

Don't just identify risks - think through consequences:

• "If X happens, then Y, which causes Z..."
• "This mitigation creates a new risk of..."
• "Solving this problem might make that problem worse..."

Competitive Response Modeling

For each competitive advantage claimed:

• "How would the top competitor respond if we succeed?"
• "What prevents them from copying this in 3 months?"
• "Do they have resources/brand to crush us even if we're better?"

Customer Psychology

Challenge solution-fit from user perspective:

• "Would I actually pay for this?"
• "What friction would stop me from buying?"
• "What objections would I have?"
• "What alternatives would I consider first?"

Integration with Conductor Workflow & Evaluate-Loop

This skill supports the Conductor methodology at two levels:

Strategic Level (Context → Spec transition)

1. Context Phase: Establish project context
2. Validation Phase: Conduct market research, competitive analysis
3. CRITIQUE PHASE (This Skill): Red team the validation findings
4. Context Update Phase: Refine context artifacts based on critique
5. Spec Phase: Define requirements for validated work

Execution Level (Evaluate-Loop support)

The loop-plan-evaluator agent uses this skill's critique framework for deep plan analysis when a plan needs strategic scrutiny beyond standard scope/overlap checks.

Loop Agent Integration:

• loop-plan-evaluator → may invoke plan-critiquer for strategic-level plan review
• loop-execution-evaluator → may invoke plan-critiquer for post-mortem analysis

The critique acts as a quality gate - don't proceed to spec/plan until critical blind spots are addressed.

Output Template

The skill uses assets/critique_template.md as the base structure. Customize sections as needed for the specific documents being critiqued, but maintain the core structure:

1. Executive Summary
2. Detailed Critique & Blind Spots (by category)
3. Action Plan (prioritized, Conductor-mapped)
4. Appendix (supporting analysis, data, references)

Tips for Maximum Value

1. Provide context: Share related documents (product.md, previous plans) so critique can spot inconsistencies
2. Be open to harsh feedback: The more brutal, the more valuable
3. Act on findings: A critique without action is wasted effort
4. Iterate: Critique → Update → Critique again for high-stakes decisions
5. Time-box: Don't let perfect critique delay necessary action - set a deadline